"I first met him when I was in middle school. Back then I used to wear ascots, and he thought that was so cool," said Matthew "Bay Bay" Williams, a Baltimore portrait artist. "He was a most interesting fellow."

Dennis Howard Lee Sherman was born in Norfolk, Va., and raised in Petersburg, Va., where he graduated from high school. During World War II, he served in the Army as a private.

After the war, Mr. Sherman studied tailoring on the GI Bill of Rights at Virginia State College in Petersburg, now Virginia State University.

Mr. Sherman came to Baltimore in the early 1950s and established himself as a tailor and necktie maker.

For years, he had Della Lou Designs, his Paca Street tailoring shop. Mr. Sherman was joined in his tie-making by his wife, the former Elizabeth Walls, whom he married in 1960.

"He was the first guy I ever knew — and even before the department stores had them — who matched his ties with pocket hankies," recalled Mr. Williams.

"He always looked neat, sharp and clean, and had his neckties and bow ties in a briefcase, and he hung around Pennsylvania Avenue and the Royal Theatre in its heyday," said Mr. Williams. "He started making ties for celebrities and entertainers."

He said everyone knew Mr. Sherman.

"I don't think he ever drove, he walked everywhere carrying his briefcase. I was busy doing charcoal sketches in the clubs when he came in," said Mr. Williams.

"He'd come in the Sphinx Club, Club Casino, Ubangi Club, Peyton Place, Bird Cage, Steve's Cocktail Lounge, Bamboo Lounge, Tijuana Club and the Alpine Villa on Harford Road," he said. "He walked up and down The Block and just didn't do bars, clubs and poolrooms; he also did churches because people got dressed up to go to church." He also covered East Baltimore clubs and churches.

Mr. Williams described him as a "very wiry guy who was liked by everyone, both black and white."

"He'd go in the roughest joints," he said, seemingly unfazed by the characters he found there. "I never, ever heard him curse."

"He'd go to businesses and even City Hall," said his daughter, Virginia Rebecca Sherman. "Self-employed, this is how he provided for his family. A particularly fond memory of his unselfishness is how he would come home, count his money, and put all of his evening earnings up on the kitchen shelf."

Mr. Sherman made custom suits for entertainers, including James Brown, and ties for Colts legend Lenny Moore, said Ms. Sherman, who teaches media at Digital Harbor High School and lives in Baltimore.

"Back in the 1950s and 1960s, a lot of big singing groups played the Royal, like the Drifters, Orioles, Cadillacs, Impressions, Softones and 'Tiny' Tim Harris," said Mr. Williams. "He really put his heart into it because no one else was doing what he was doing."

Even though Mr. Sherman made suits and vests from time to time for Mr. Williams, "accessories seemed to be his primary interest. It was his niche," he said.

Mr. Williams praised his friend's work ethic — at one time, in addition to his necktie making and tailoring shop, he owned and operated Tiny Tim's, a carryout.

"He was very astute in so many ways and was very bright. He belonged to a time and era when there was prejudice, and he had to go and get it for himself," he said. "He had a spirit and was his own boss. He would do whatever he had to do and was always the consummate gentleman."